Why the Best Attorneys Are So Hard on Themselves and Others

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By nature, lawyers are perfectionists.

That makes them expect perfection from themselves and others.

Keep reading to see why perfection is hard to achieve and why attorneys expect perfection from those around them.

The first job I ever had was as an asphalt contractor in Grosse Pointe, Michigan. Grosse Pointe is an area of about 25,000 people that is socially stratified between middle class and very wealthy people. The city is built along the shores of Lake St. Claire. The wealthiest families tend to live along the lake. As you move away from the lake the houses get smaller and smaller until you arrive in Detroit—which is very poor.

Asphalt cracks in the winter in cold climates, which causes it to break up and look bad, so each year people from all wealth brackets were happy to have me work on their driveways. This was a source of income that kept me busy all summer. I generally would start my summers working on the larger lakefront homes and move inland as the summer progressed.

First, I would make the most money and have the least stress doing the work for the people on the “poorer streets” farthest from the lake. The less wealthy people would not bargain about the cost as much, were less critical, paid faster and were easier to work with. Moreover, they generally were very nice people and easy to work with. They would also make decisions about doing the work quite quickly—the same day I came around trying to sell them the work.

In contrast, working for the wealthiest people with mansions was very unpleasant. They would take a long time to decide whether or not to have the work done. They would ask for references. They would bargain the price down to a level where I did not make much money. They would micromanage the projects. They were highly critical of the work when it was being done and after. They would bargain about the price after the work was done. They would withhold payment for inconsequential reasons. They would complain and itemize their complaints about inconsequential things in writing. All in all, they were extremely difficult to work with and I rarely made much money despite the giant sizes of the jobs. The wealthy people would crush my self-esteem and they were extremely good at it.

I started to understand something early on: The most successful and wealthiest people are the most demanding and the hardest to work for. They are also wealthy (most likely) because of their high standards and because they are able to see so much of what is going on around them.

Someone I knew once worked directly for a well-known billionaire. She had been working for him for over a year and thought that everything was going very well. Then one day as she was going about her business he walked up to her and spent 10 minutes telling her countless inconsequential things that she had done wrong. She broke down and started crying. She had no idea he was aware of these things.
They included such items as ordering one more box of pencils than was needed and “wasting” his money. It was the level of detail he was able to go into with her that frightened her. She realized, like I did, that the most successful people are often the most judgmental and see more of what is going on.

Powerful and wealthy people are more likely than not on top of every single detail. They are incredibly difficult to work for, they have very high standards and will milk you for all that you are worth if they can. This level of judgment and the amount of details that are seen is one of the main contributors to their success.

Near the height of his fame in 1993, Michael Jackson told Oprah Winfrey that he was never pleased with his work.

He was so judgmental with himself that it is likely that his self-criticism may have led to depression, unhappiness and the overmedicating that ultimately contributed to his death. Many stars and others are so judgmental with themselves that they find ways to dull the voice inside of them by using drugs and other distractions and this ends up killing them. When you hear about Prince and other stars that drugged themselves to death, what do you think it is that leads to this?

Do you see any similarities to what it is like working for very wealthy people to what it is like working in a large, demanding law firm, or for powerful attorneys?

Prestigious law firms:

Represent powerful, wealthy people and companies and these clients are incredibly demanding.

Are very hard to get jobs with.

Are often not very nice people.

Will take all they can from you.

After a period of doing asphalt work for the wealthiest people, the smartest thing may have been to switch my focus and just work for people who were less demanding (and where I made less money). My sanity and happiness should have demanded that I work for people who were not going to treat me so poorly and make life so difficult. Life is too short and a good decision for me might have been to avoid the people who were going to be difficult to work with. Everyone I was in competition with wanted to work on the largest homes—it was more prestigious to work for the wealthiest people! I decided to follow the crowd and try to work for the wealthiest and most successful people. I detested the criticism and high standards but I knew there must be something to it.

But the high standards I demanded of myself made me better at my job. I developed new systems to get better and better at what I was doing. I started getting recommended by the wealthy people for larger jobs. I became more and more successful, my confidence increased and I started getting into situations that were even harder than working for homeowners. Soon I was working on roads and other major projects that presented much more extreme challenges. There were more unknowns and money at stake.

When I started practicing law—like most attorneys—I went to work for the most demanding attorneys and law firms I could find. It was no different than working for the rich people on their driveways and the standards demanded were incredibly high. I understood instinctively from my asphalt experience what was going on; however, I cannot say I enjoyed it any more. When you are an associate in a large law firm you are selling something and being used to extract the maximum amount of value that can be extracted. Your choice is to embrace this world and way of being or leave. Most people leave. Some even leave the practice of law all together—which is often a huge mistake. I will have more on that shortly.

Your choice when faced with your own happiness may often appear to be to leave the judgmental demanding environment or remain. These are two choices and something that attorneys often do. They look for in-house positions, or positions where they are not going to be judged and evaluated harshly. They believe that this will lead to happiness and for some it does.

In most cases, attorneys desire positive feedback. You generally need to have academic drive and skill to become an attorney to begin with. Teachers and parents encourage future lawyers at a young age to do well in school and reward and punish them depending on how they do. They are competing and reaching for the best grades and want to impress others with their performance. They fear the consequences of not doing well in terms of how they will feel about themselves and what will happen to them.

Someone I know recently moved to Central America to retire because it is “cheaper.” However, the person is not poor. This person worked in a decent job and managed to save a few hundred thousand dollars—but had always dreamed of being “rich and successful.” This person took a variety of “get rich seminars” to try to learn how to make a bunch of money. This person never felt successful enough. Now, this person is living in a remote area of Central America where people do not speak English, people are very poor and this person feels wealthy as a result of being surrounded by poor farmers in the middle of nowhere.

“It’s the best move I ever made,” the person told me. “I am so much happier here not having to worry about whether I am keeping up with everyone. I finally feel like I have made it.”

We spoke through a videoconferencing application and I could scarcely believe what I was seeing and hearing. In the background I could hear all sorts of exotic birds and other creatures (which sounded like monkeys) making noises. The person appeared to be in a home on stilts in the middle of the jungle. Instead of windows there were shades that were closed at night and there were a bunch of fans going on the ceiling.

But I do not think this person is happy—having gone from living in Chicago to surviving in the jungle. This person is away from family and friends. What this person is really doing is running away from feeling judged and unhappy for not being who the person wanted to be in the United States.

I keep thinking about the statements “not having to worry about whether I am keeping up” and “I finally feel like I made it” because there is so much to these statements. The person flat out got up and moved outside the United States, to a completely unfamiliar environment, in order to feel successful. Feeling financially successful and superior to others was that important to this person. This person wanted to feel important so much that they moved to a third world country.

The more I thought about this, however, the more I realized that attorneys do a version of this all the time. No one likes to constantly feel “less than.” No one likes constant criticism. No one likes to be reminded that they are not the best.

However, for attorneys the pain of this is much more severe than for most people because attorneys are disproportionately driven to be extremely successful. They are driven to put themselves in extremely competitive environments where they are criticized and can never feel as successful as they would like to feel. Because they are so status and money conscious, many attorneys end up leaving the practice of law completely—or finding areas where they are not going to be judged as harshly and the standards are lower.

One of the most distressing aspects of my job is that I tend to spend the day finding reasons why people are not good enough. This is something I have to do. I look at resumes, speak on the phone and take people apart to find reasons why they do not meet the high standards of law firms, or are going to be unlikely to succeed inside of a major law firm. In my current job I am not different that the wealthy man in his lakeside home finding 20 reasons why I did a bad job and could do better on his driveway.

I am not proud of any of this. I am basically just someone who knows what law firms want and make these sorts of distinctions for them. This is the same thing that admissions officers in schools do, that talent agents do, that employers do and others do. It is the same thing that schools do with grades, that people do socially (including and excluding people) and that the people we are romantically interested in do (rejecting, accepting, or reluctantly accepting us). All around us we are constantly being judged, ranked and sorted and it is no fun.

I have been doing this going on two decades and have a very good understanding of this and can pick up a resume and size up a candidate very quickly. I can enrage and make a lifetime enemy out of an attorney who thinks he or she is very successful in less than a few minutes by pointing out why he or she is not going to last in a major law firm. This happens all the time. People call me with a healthy self-esteem believing they can work anywhere and I have to tell them that this is an impossibility.

I received the below email while writing this article and receive several similar ones throughout a typical day:

I receive emails like this quite often—just about every single day. I write about the job market and why attorneys are and are not marketable to prestigious law firms. I also tell attorneys why I cannot help them find positions in prestigious firms.

When we make judgements about others, though, judgment comes back to us and people attack. People who judge others for a living (and most attorneys do) also end up judging themselves. Attorneys receive some of the harshest criticism and judgement of any profession. They are in a profession that has all sorts of rules and distinctions and seems to constantly be keeping them down. Attorneys work very hard and want positive reinforcement (like they received in school) and yet they often are met every step of the way with the exact opposite. Attorneys feel constantly judged and they are.

They are judged by clients.

They are judged by bosses.

Litigators are judged by judges.

They are judged by opposing counsel.

In fact, everywhere an attorney turns the attorney will find that he or she is being judged by someone. This criticism takes its toll. It is difficult when criticism comes in all directions and never stops. It is extremely difficult being an attorney when everywhere you turn there is criticism. It leads to unhappiness and depression. It is why attorneys are unhappy and feel the need to escape.

In fact, everywhere you turn you will find countless messages that you are not good enough. The legal market is incredibly competitive and the feedback many attorneys receive is not so great for their self-esteem. It is downright painful and not fun. Everyone is judging you all the time.

This judgment is incredibly stressful.

You cannot bill enough hours.

You cannot have enough business.

You cannot go to a good enough law school.

You cannot do well enough in law school.

You cannot do enough and are constantly under attack as a result.

The world appears to always be pushing you down and forcing you to get up and stand up higher and higher.

The problem with practicing law for most attorneys is not the work itself, it is how attorneys judge themselves because of the way their environment judges them. This is what makes them unhappy. It is the voice inside the attorney’s mind that is constantly telling the attorney that he or she is not good enough that creates the problems with practicing law.

Most attorneys who last for more than a few years inside of a law firm are competent and can do the work. Most may even enjoy the work itself. What creates the most problems for attorneys is the way they constantly judge themselves. They compare themselves to others. The enemy of most attorneys is if the voice inside their heads. This is what makes them unhappy.

Being the very best you can be may seem like a good thing; however, when you are constantly judging you are going to find fault in every small thing out there. You are going to suffer from having massive expectations for yourself that you can never meet. You will likely become depressed. This mindset can harm your health. While it is anecdotal, most of the people I know who have gotten sick and died from cancer were the most self-critical. Ironically, Chet Holmes (my mentor) died of cancer at a young age as well and was incredibly judgmental with himself. There are far ranging health problems for people who strive for perfection and judge themselves too harshly.

My mentor, the late Chet Holmes (a well-known business consultant), came to my company Christmas party one year and met a bunch of employees of mine. He met one girl who was about 18 years old, had not finished high school and worked in a customer service role answering phones. He spent about 5 minutes with her.

“You need to put her in a sales position. She is amazing!” he told me.

“Why?”

“Because she does not give a shit. Nothing will phase her. She is incredible.”

I listened to him and within 6 weeks she was making $10,000+ a month when she had formerly been making only $10/hour. Never in my or her wildest dreams could I have expected this girl to be so successful. People would throw all sorts of negativity and criticism at her and she would just keep going. It was as if nothing had happened at all. She literally did not care. Nothing upset her and she just kept picking up the phone and calling people.

The most successful salesman I know (who makes over $10,000,000 a year selling), told me that the difference between him and others who do his job is “ego.” He does not involve his ego in the least in what he is doing. He does not care. By eliminating his ego he puts himself in a position where he succeeds where others allow their minds to play tricks on them.

I am not sure “not giving a shit” would ever work in a law firm because that is the exact sort of place where you need to “give a shit” about every single detail. There is something to this, though. If you do not care what other people think of you, and are not judgmental with yourself all the time then you are likely to also be less hard on yourself. Being less hard on yourself will result in you being happier and even more productive—you will not be worrying about what others think about you and will, instead, be in a position to succeed.

This is some of the most important advice you will ever receive about working in a law firm because it can make the difference between being happy and not being happy. You do not necessarily need to go in-house, or escape. You need to get your mind right and realize it is all a game. You need to keep your mind clean to play the law firm game.

You might find this hard to believe, but I get on the phone with a professional business consultant for an hour two times each week and I pay him to criticize me and my business. I literally get on the phone and listen to two hours worth of criticism. I then have him do this with other managers in my company each week as well.

I generally get off of these conversations extremely unhappy as the things I am doing wrong are all laid out for me. It is no fun being criticized and judged. This criticism about what needs to be improved is often so substantial it gets me up at night, but it makes me up my game and get better at what I do. It also makes the service the company provides much stronger for our candidates because I am willing to listen. Far from thinking I am important, I am always made to feel like I am behind. The consultant does not know it, of course, but the second he tells me I am doing very well he will have lost his job working for me.

You will be happier if you decide not to put yourself in judgment’s way, but you need judgment and criticism to improve and stay on your toes. The best thing you can do for yourself is to take what comes at you and try to improve, while staying happy. You never want to stop putting yourself in the direction of judgment or criticism, because this is where mediocrity and a lack of success lie. You need to ask yourself if you want to live on the lake, or in the bad part of town.

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